This is certainly possible. Consider $f:\Bbb R\to\Bbb R$ with $f(x):=x^2$. Then the image $4$ has preimage $\pm 2$. Indeed, for any $y>0$ there are two preimages under $f$, i.e. $\pm\sqrt y$. Another example is $g:\Bbb R\to\Bbb R$ with $g(x):=\sin(x)$. In this case, for any $-1\leq y\leq 1$ in the image, there are infinitely many preimages for $y$ under $g$ (due to the periodic nature of $g$).
When a function has a unique preimage for every element of the image, we say that the function is injective. Perhaps you've heard of the "vertical line test" for a function; well the "horizontal line test" determines whether a function is injective or not (when it can be plotted on the Cartesian plane).
I will note that $h:\Bbb R\to\Bbb R$ with $h(x):=\sqrt x$ is actually injective, and therefore has a unique preimage for every image. Indeed, $\sqrt x=\sqrt y\implies x=y$.